Family-friendly holiday rentals in Hillcrest

An inviting outdoor area is presented featuring a cozy sectional sofa with colorful cushions. Lounge chairs in light blue are positioned beside a palm tree, with soft lighting illuminating the space. An orange umbrella provides shade, creating a comfortable setting for relaxation.

4.93 out of 5 average rating, 166 reviews

Light & Airy Craftsman in Mission Hills/Hillcrest

This craftsman, built in 1923, was recently updated with modern finishes throughout! It includes a vaulted ceiling in the great room and plenty of outdoor spaces in the fully-fenced in yard, in addition to an outdoor shower to clean up after the beach. The open main room has areas for all your needs: fully stocked kitchen with gas stove, dining area, two-person breakfast counter, living room with flat screen TV, and an office area with two computer monitors & a keyboard for your personal use.

A bright living space features a warm wooden ceiling and large windows. A comfortable orange sofa is paired with a wooden coffee table on a patterned area rug. The kitchen, visible in the background, includes modern appliances and white cabinetry, enhancing the cozy atmosphere.

4.99 out of 5 average rating, 180 reviews

1 bedroom, 1 bath /Hillcrest/San Diego Zoo/Balboa

One bedroom, one bath with a pool in the Hillcrest/San Diego Zoo/Balboa Park /Marston Hill area. Full kitchen, queen bed, queen sleeper sofa & crib. Indoor/outdoor dining, WiFi, smart TV, pool, AC/heating, BBQ& free parking. Walking to restaurants/bars/shops/stores (Trader Joe's, Ralph's & Whole Foods). Walking to the Farmers Market. Minutes' drive to all San Diego beaches. No rent for children under 3, only a $95/stay flat fee. High chair, Pack & Play Crib, crib mattress & cover are provided

4.97 out of 5 average rating, 425 reviews

A sunlit living area features two comfortable armchairs facing a glass coffee table with books and magazines. Large windows are adorned with light curtains, and a decorative lamp adds warmth. A dining table with chairs is positioned nearby, creating a cozy gathering space.

Bungalow in Hillcrest

Vintage Spanish Revival Home - Balboa Park - Alcazar Court

• 1924 Spanish Revival Bungalows - Alcazar Court - Nestled in the heart of the city in historic Hillcrest - with cafes, bars, and shops • Fully equipped 1 bd 1 ba bungalows complement shady olive tree-lined patios - guests can enjoy coffee in the morning - a glass of wine in the afternoon. Enjoy the charm and tranquility of a bygone era and convenience of modern amenities, • Explore nearby Balboa Park, home to 16 museums and performing arts venues, as well as the world-famous San Diego Zoo.

4.96 out of 5 average rating, 118 reviews

The living area features a spacious sectional sofa facing a modern television mounted above a stone fireplace. A round white coffee table is positioned centrally on a polished floor, while a potted plant adds a touch of greenery. Natural light floods in through the large window.

Home in San Diego

Central Charm in Hillcrest near Scripps Mercy

Your family will be close to everything when you stay at this centrally-located place, making it the perfect home base for your San Diego adventures. Walk to Hillcrest's vibrant heart, where you’ll find a wide variety of restaurants, bars, and shops at your doorstep. Enjoy easy access to Balboa Park and the world-famous Zoo, just minutes away! Explore nature and culture with ease. This clean-cut, cozy 3-bedroom home offers a relaxing space to unwind after a day in the city. Recharge in comfort,

An outdoor dining area features a dark wood table surrounded by four chairs, set against a backdrop of lush greenery. A large umbrella offers shade, while warm lights illuminate a nearby tree. The space is designed for relaxation and enjoyment.

4.95 out of 5 average rating, 265 reviews

Stunning Grand Villa Dream Yard Amenities Location

Stunning Grand Villa in the perfect Location with Amazing Amenities!! Relax and recharge in this beautifully designed home featuring a hot tub, soaking tub, peaceful Zen garden, fully fenced yard, gated parking, luxury Posturepedic mattresses, grill, central A/C, fast WiFi, parking, and a fully stocked kitchen. Located In Marston Hill next to Balboa Park and the Zoo, minutes from San Diego’s top beaches and attractions, and walking distance to an incredible selection of restaurants and shops.

Home in University Heights

4.92 out of 5 average rating, 179 reviews

Cozy 2 bed 1 bath Bungalow!

2 bed 1 bath cute bungalow, this 800 square foot house sits on a 6,996 square foot lot with all the amenities you need for a comfortable stay! The cozy bedrooms adjoin the bathroom, the living room has a large TV with Roku remote. Washer & dryer available for use in the kitchen, dine inside or BBQ on the patio in the backyard. Enjoy your morning coffee on the front porch taking in this nice neighborhood! You're very centrally located in a walkable neighborhood with many local hotspots nearby.

Guest suite in University Heights

A charming cottage is set within a lush garden, featuring a variety of tropical plants and vibrant flowers. The pathway leads to the entrance, framed by palm and cacti, inviting guests to explore the serene outdoor space.

4.98 out of 5 average rating, 824 reviews

MIKE'S PLACE - A PRIVATE COTTAGE

The cottage features full amenities that include: Tempurpedic™ queen-size bed. Wi-Fi, Smart TV, air conditioning, refrigerator, microwave, wet bar, coffee maker, toaster, and iron. Window seat for sitting, reading or lounging. Private entrance and patio connecting to a courtyard and Japanese garden. Spacious bathroom with 12 foot high tiled shower. French doors open to a private sitting area. If the days are booked in the cottage we might have an opening at, Mikes House and Garden.

4.96 out of 5 average rating, 254 reviews

A bright living area features a comfortable light gray sofa adorned with decorative pillows. A round coffee table sits on a patterned rug, and a wall-mounted television is visible. Natural light filters through a large window beside the front door, which is framed with greenery.

Cottage in Hillcrest

Canyon Views w/ Outdoor Seating & Parking

Prime location! Within walking distance to Trader Joe’s, Whole Foods, Ralph’s, cafes, gyms, amazing restaurants, great nightlife, and Sunday's Farmer's Market! This newly restored historic cottage is in the heart of Hillcrest, San Diego. Originally located in Balboa Park, it housed workers for the 1915 Panama–California Exposition. Perched on a canyon, the cottage blends modern amenities with farmhouse charm. Book now for a San Diego stay that fuses the past with modern comforts!

Bungalow in Greater North Park

The inviting entrance features a covered porch adorned with a vibrant yellow door. Succulents and greenery enhance the landscape, complemented by a palm tree nearby. The porch area includes seating, providing a welcoming atmosphere for relaxation.

4.96 out of 5 average rating, 164 reviews

The Cozy Craftsman

Bright • Walkable • Charming 2BR Craftsman retreat in San Diego's University Heights neighborhood, perfectly located between Hillcrest and North Park. Skylights and large windows fill the home with natural light, while the thoughtfully updated interior offers comfort and style. Enjoy a private fenced yard with outdoor seating, and walk to restaurants, cafes, and a grocery store just two blocks away. Perfect for couples, small groups, or business travelers exploring San Diego.

5 out of 5 average rating, 142 reviews

A private outdoor seating area is showcased on a rooftop terrace, featuring two armchairs and a spacious couch, all adorned with decorative cushions. A wooden coffee table sits in the center, surrounded by lush greenery and palm trees. The sunset casts a warm glow over the scene.

Guest house in Hillcrest

Rooftop views 10min walk to Balboa Park/Zoo/Bars

Enjoy this peaceful second-story new guesthouse overlooking the treetops! A perfect day might be a morning stroll through Balboa Park, the cultural center of San Diego, surrounded by 58 miles of walking and running trails, followed by a short walk to the super fun bars and restaurants of Hillcrest, North Park, and University Heights. We LOVE this neighborhood and we are so excited to share the beauty, culture, and welcoming vibe of it with our guests!

Home in University Heights

A charming historical home is portrayed with a welcoming front porch and steps leading to the entrance. Lush greenery surrounds the property, with a hammock suspended between two trees. Bright sunlight filters through the leaves, highlighting the inviting atmosphere of the exterior.

4.98 out of 5 average rating, 108 reviews

Cozy & Quaint... blocks from Contemporary & Cool

This beautiful, historical home in charming and quiet University Heights is a 5 min walk to the heart of Hillcrest. Pride anyone? For those into Comic-Con, it's only a 10 minute drive to The Gaslamp District/ Convention Center! Take advantage of the central location within a short distance of great dining, entertainment, and night life. Balboa Park is just a mile. ... or enjoy your time around the house with the many options for outdoor relaxation.

A charming craftsman bungalow is presented, surrounded by lush greenery and flowers. The inviting exterior features a covered porch and multiple large windows that provide natural light. The structure maintains its classic architectural style while nestled in a tranquil neighborhood.

4.95 out of 5 average rating, 126 reviews

Bush Street Home in San Diego

Welcome home! A spacious & open floor plan, this renovated craftsman home has 2 bedrooms & a bath. From a cozy living room with a smart TV & a fully equipped kitchen, you can make yourself at home knowing you’ll have a cozy place to relax after sight seeing & make the most of your home-away-from-home. Close to downtown San Diego, Balboa Park, Gaslamp, Little Italy, walking distance to Hillcrest & many restaurants, coffee shops and grocery stores.

Popular amenities for Hillcrest family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Guest suite in Greater North Park

A spacious guest suite is featured, showcasing a comfortable bed and a stylish seating area. Natural light illuminates the room, highlighting a modern sauna enclosed in glass. Elegant decor is complemented by a chandelier, adding a touch of sophistication to the inviting atmosphere.

5 out of 5 average rating, 105 reviews

Hidden Spa w/ Sauna and Hot Tub near Balboa Park

The exterior of a Spanish-style house is presented with warm earth-toned walls and vibrant tiles leading up to the entrance. Lush landscaping features palm trees and other native plants, creating an inviting ambiance. A wooden garage door complements the overall aesthetic, enhancing the home's charm.

4.91 out of 5 average rating, 403 reviews

Stunning Home w/ Private Hot Tub - Outdoor Living!

Guest house in Mission Hills

A cozy sleeping area features a spacious bed with a striped throw blanket adorned with decorative tassels. A flat-screen TV is mounted on the wall, and a small table is positioned beside the bed. Soft lighting is provided by wall sconces, creating a calm ambiance.

4.91 out of 5 average rating, 501 reviews

Mission Hills Charming suite, walkable to all.

An inviting outdoor area features a modern infinity pool, surrounded by lush greenery. Comfortable seating in blue upholstery invites relaxation, while sun loungers provide additional spaces for sunbathing. The serene atmosphere is enhanced by the tranquility of nature in the background.

4.91 out of 5 average rating, 172 reviews

Pool Oasis in Central Hillcrest by Park/Zoo

Guest house in Mission Hills

A spacious living area features a large sectional sofa adorned with decorative pillows, complemented by a wooden coffee table. A vibrant wall art piece with colorful surfboards is displayed above the couch, while natural light fills the room through expansive windows.

4.97 out of 5 average rating, 288 reviews

Beautiful Historic Home and Gardens Near Downtown!

5 out of 5 average rating, 171 reviews

Top 1% Hot Tub Oasis Walkable North Park

A private hot tub is positioned on the outdoor terrace, with a panoramic view of the city at dusk. Soft lighting from the surrounding area creates a relaxing atmosphere, while patio furniture and an umbrella are visible nearby. Large sliding doors provide access to the indoor living space.

4.97 out of 5 average rating, 137 reviews

The California

4.93 out of 5 average rating, 361 reviews

The open living area features a dining table with modern chairs and a sectional sofa. Artwork adorns the walls, and large windows allow natural light to fill the space. A cozy bedroom is highlighted by a stylish chandelier and a plush bed, complemented by decorative tiles in the bathroom.

Home in Normal Heights

NEW❤️Special Deals/HotTub/Firepit/private yard/BBQ

Family- and pet-friendly home rentals

Flat in Greater North Park

A charming casita exterior features a light-colored facade with green shutters. A tiled staircase leads to the entrance, flanked by vibrant landscaping. A garage door is visible, and a pathway is lined with plants, set against a clear blue sky.

4.96 out of 5 average rating, 181 reviews

Modern Spanish Casita. Sunny & Quiet with Kitchen!

Flat in University Heights

A cozy living room features a yellow armchair and a sleek coffee table. Natural light filters through sheer curtains, illuminating the space. A flat-screen TV is positioned on a modern media console, beside decorative items including a tall potted plant and a small basket.

4.93 out of 5 average rating, 135 reviews

Bright Oasis in the Heart of University Heights

A well-equipped kitchen features a charming wooden island with bar stools, surrounded by modern appliances. Light streams through multiple windows, illuminating the cozy living area visible in the background. The warm tones of the wood beams and flooring enhance the welcoming atmosphere.

4.96 out of 5 average rating, 157 reviews

Beautiful Canyon Cottage located on a huge lot

Superhost

The kitchen features modern wood cabinetry complemented by dark granite countertops. A stainless steel refrigerator stands next to a gas oven, with a microwave positioned above. Cooking essentials like a coffee maker are visibly arranged, providing convenience for meal preparation.

4.82 out of 5 average rating, 745 reviews

Craftsman Home, large deck. Walkable, Views!

Superhost

The living room showcases a spacious sectional couch with a chaise, paired with a sleek armchair. Natural light is welcomed through large windows, highlighting the warm hardwood flooring. Decorative elements include a coffee table and a soft rug, enhancing the inviting ambiance.

4.86 out of 5 average rating, 352 reviews

Modern House In The Hills | Killer Location!

Guest suite in Greater North Park

The kitchen features modern appliances, including a stainless steel oven, microwave, and refrigerator. A central island with two bar stools provides a cozy dining space. Natural light fills the room, highlighting the sleek cabinetry and patterned area rug, creating an inviting atmosphere.

4.99 out of 5 average rating, 316 reviews

Walkable North Park Casita

A modern living space features a stylish blue sofa paired with a glass coffee table. A sleek armchair and colorful wall art enhance the decor. The open layout connects to the kitchen, showcasing upgraded appliances in a welcoming atmosphere, with soft lighting flooding the room.

4.93 out of 5 average rating, 151 reviews

California Dreaming 2-Charming/Modern 2BD, 1 Bath

An outdoor patio area showcases a modern gas fire pit with flames reflecting off the smooth surface. A spacious bed is visible through large glass doors, framed by stylish curtains. The warm tones of the interior including a wooden accent wall create a cozy atmosphere.

4.97 out of 5 average rating, 271 reviews

Ventana Vista | Ocean View | EV Charger | Designer

Family-friendly home rentals with a pool

4.99 out of 5 average rating, 156 reviews

3BR Urban Oasis with Hot Tub, Pool & Private Deck

5 out of 5 average rating, 221 reviews

A serene backyard is framed by colorful sunset skies, featuring a cozy hammock in the foreground and a comfortable seating area with grey couches. String lights add warmth to the outdoor space, complemented by lush greenery throughout the neatly landscaped yard.

Home in La Jolla

La Jolla Beach House-Family Focused-3min to Beach

4.97 out of 5 average rating, 115 reviews

A serene pool area features a cascading waterfall illuminated in soft purple hues. The water flows gently into the heated pool, adding a calming effect to the ambiance. Wood paneling surrounds the pool, creating a private and tranquil atmosphere.

Villa in San Diego

Lux Villa: Heated Pool, Sauna, & Gym

Flat in Greater North Park

A serene bedroom features a queen bed with a light-colored quilt. Two bedside tables with lamps are positioned on either side. The walls are adorned with various framed artworks and a large mirror, reflecting natural light from the windows.

4.79 out of 5 average rating, 476 reviews

On park. 1 bed apt.has air & small kitchen+w&d

A vibrant heated pool is surrounded by minimalistic landscaping, featuring tall cacti and a clean white fence. Soft lounge chairs are positioned nearby for relaxation. The clear water reflects the blue sky, creating a refreshing setting for leisure and enjoyment.

4.93 out of 5 average rating, 285 reviews

Lionhead - Private Boutique Home

An outdoor living space is showcased, featuring a circular pool surrounded by wooden decking. Comfortable lounge seating with dark cushions and a fire pit is positioned under string lights. Umbrellas provide shade while a gas grill is visible nearby, creating an inviting atmosphere.

4.95 out of 5 average rating, 192 reviews

Luxury Family Home Near Dining, Shops + Zoo

4.93 out of 5 average rating, 138 reviews

A living room features a luxury hanging chair suspended from the ceiling. Natural light filters through sheer curtains, illuminating a cozy seating area with a plush sofa and wooden coffee table. A 50” television is mounted above an elegant fireplace, enhancing the room's comfort.

Home in City Heights

Designer Luxury Rental With Pool